The catalytic addition of N-H bonds to olefins (eq.(I)) to yield amines is a process of potentially great technological importance. ##STR1## However, presently known catalyst systems, employing palladium, platinum, or alkali metal catalysts, can be relatively inefficient, having very low rates, poor catalyst lifetimes, poor selectivities, or requiring initial modification of the amine--e.g., tosylation. As a result, many current catalytic processes involve the conversion of alcohols to amines with the alcohol, which in turn, is prepared from the olefin. Such hydroamination reactions are exothermic, yet thus far have proven difficult to perform due to a lack of suitable catalysts and, to a lesser extent, unfavorable entropy effects. As a result, more attention has been paid to aminating olefins intramolecularly, and limited successes have been experienced in both stoichiometric and catalytic type reactions. A rapid efficient, direct process for the hydroamination of olefins would be beneficial.
Organolanthanide catalysts have been found useful as noted in U.S. Pat. No. 4,668,773 to Marks and Mauermann, the organolanthanide complexes [.eta..sup.5 --(CH.sub.3).sub.5 C.sub.5 ].sub.2 MCl.sub.2 --Li](C.sub.2 H.sub.5).sub.2 O].sub.2.sup.+, M=La, Nd, Sm, Lu, with LiCH[Si(CH.sub.3).sub.3 ].sub.2 were shown to provide a straight-forward route to ether-free and halide-free bis(pentamethylcyclopentadienyl) lanthanide alkyls [.eta..sup.5 (CH.sub.3).sub.5 C.sub.5].sup.].sub.2 MCH[Si(CH.sub.3).sub.3 ].sub.2. Such [.eta..sup.5 (CH.sub.3).sub.5 C.sub.5 ].sub.2 MCH[Si(CH.sub.3).sub.3 ].sub.2 complexes react with H: under mild conditions to yield the corresponding hydrides [.eta..sup.5 (CH.sub.3).sub.5 (C.sub.5).sub.2 MH[.sub.2. These complexes have been found to be extremely active homogeneous olefin polymerization catalysts, as well as catalysts for olefin and acetylene hydrogenation.